# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_0914161_0m
_database_code_depnum_ccdc_archive 'CCDC 1848338'
_audit_update_record             
;
2018-06-09 deposited with the CCDC.
2018-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H54 Co3 N12 O6, 2(C H4 O), 2(Cl)'
_chemical_formula_sum            'C56 H62 Cl2 Co3 N12 O8'
_chemical_formula_weight         1278.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   11.349(2)
_cell_length_b                   11.349(2)
_cell_length_c                   38.211(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4262.4(17)
_cell_formula_units_Z            3
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    1484
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.67

_exptl_crystal_description       platelet
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             1983
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.025
_shelx_estimated_absorpt_T_min   0.821
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9474
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         2.330
_diffrn_reflns_theta_max         28.526
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2353
_reflns_number_gt                2014
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2353
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1645
_refine_ls_wR_factor_gt          0.1559
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.6667 0.3333 0.26156(2) 0.0097(2) Uani 1 3 d S T P . .
O1 O 0.5680(2) 0.3779(2) 0.29422(5) 0.0111(4) Uani 1 1 d . . . . .
C1 C 0.4458(3) 0.3666(3) 0.28938(8) 0.0127(6) Uani 1 1 d . . . . .
C2 C 0.4108(3) 0.4448(3) 0.31035(8) 0.0177(7) Uani 1 1 d . . . . .
H2 H 0.4720 0.5017 0.3279 0.021 Uiso 1 1 calc R U . . .
C3 C 0.2880(4) 0.4404(4) 0.30580(9) 0.0237(7) Uani 1 1 d . . . . .
H3 H 0.2658 0.4949 0.3201 0.028 Uiso 1 1 calc R U . . .
C4 C 0.1968(4) 0.3570(4) 0.28050(10) 0.0257(8) Uani 1 1 d . . . . .
H4 H 0.1129 0.3551 0.2772 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2290(3) 0.2767(4) 0.26012(9) 0.0201(7) Uani 1 1 d . . . . .
H5 H 0.1656 0.2180 0.2432 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3538(3) 0.2801(3) 0.26392(8) 0.0151(6) Uani 1 1 d . . . . .
C7 C 0.3868(3) 0.1973(3) 0.24099(8) 0.0127(6) Uani 1 1 d . . . . .
N1 N 0.2896(3) 0.0905(3) 0.22298(8) 0.0180(6) Uani 1 1 d . . . . .
H1 H 0.224(4) 0.082(4) 0.2199(10) 0.017(11) Uiso 1 1 d . . . . .
C8 C 0.3527(3) 0.0431(3) 0.19754(9) 0.0179(7) Uani 1 1 d . . . . .
H8 H 0.3506 0.0758 0.1736 0.022 Uiso 1 1 calc R U . . .
H8A H 0.3083 -0.0574 0.1974 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4976(3) 0.1087(3) 0.21180(8) 0.0148(6) Uani 1 1 d . . . . .
H9 H 0.5119 0.0417 0.2249 0.018 Uiso 1 1 calc R U . . .
H9A H 0.5650 0.1470 0.1926 0.018 Uiso 1 1 calc R U . . .
N2 N 0.5088(2) 0.2175(3) 0.23521(7) 0.0116(5) Uani 1 1 d . . . . .
Co2 Co 0.6667 0.3333 0.3333 0.0106(3) Uani 1 6 d S T P . .
Cl1 Cl 0.0000 0.0000 0.19352(3) 0.0153(3) Uani 1 3 d S T P . .
C10 C 0.3333 -0.3333 0.2191(7) 0.135(7) Uani 1 3 d S T P . .
H10 H 0.3832 -0.3183 0.2411 0.203 Uiso 0.3333 1 calc R U P A .
H10A H 0.2399 -0.3552 0.2241 0.203 Uiso 0.3333 1 calc R U P . .
H10B H 0.3784 -0.2508 0.2047 0.203 Uiso 0.3333 1 calc R U P . .
O2 O 0.3312(15) -0.4428(18) 0.2007(10) 0.184(16) Uani 0.3333 1 d . . P A -1
H2M H 0.2612 -0.4810 0.1881 0.276 Uiso 0.3333 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N2 1.896(2) 2_655 ?
Co1 N2 1.896(2) 3_665 ?
Co1 N2 1.896(3) . ?
Co1 O1 1.906(2) . ?
Co1 O1 1.907(2) 3_665 ?
Co1 O1 1.907(2) 2_655 ?
Co1 Co2 2.7427(8) . ?
O1 C1 1.340(3) . ?
O1 Co2 2.076(2) . ?
C1 C2 1.393(4) . ?
C1 C6 1.406(4) . ?
C2 C3 1.380(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.463(4) . ?
C7 N2 1.305(4) . ?
C7 N1 1.350(4) . ?
N1 C8 1.461(4) . ?
N1 H1 0.71(4) . ?
C8 C9 1.527(4) . ?
C8 H8 0.9900 . ?
C8 H8A 0.9900 . ?
C9 N2 1.478(4) . ?
C9 H9 0.9900 . ?
C9 H9A 0.9900 . ?
Co2 O1 2.076(2) 17 ?
Co2 O1 2.076(2) 18_545 ?
Co2 O1 2.076(2) 16_655 ?
Co2 O1 2.076(2) 2_655 ?
Co2 O1 2.076(2) 3_665 ?
Co2 Co1 2.7425(8) 16_655 ?
C10 O2 1.42(3) 2_545 ?
C10 O2 1.42(3) . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
O2 H2M 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Co1 N2 94.43(11) 2_655 3_665 ?
N2 Co1 N2 94.43(11) 2_655 . ?
N2 Co1 N2 94.43(11) 3_665 . ?
N2 Co1 O1 170.88(10) 2_655 . ?
N2 Co1 O1 90.03(10) 3_665 . ?
N2 Co1 O1 93.16(10) . . ?
N2 Co1 O1 90.03(10) 2_655 3_665 ?
N2 Co1 O1 93.16(10) 3_665 3_665 ?
N2 Co1 O1 170.88(10) . 3_665 ?
O1 Co1 O1 81.77(9) . 3_665 ?
N2 Co1 O1 93.16(10) 2_655 2_655 ?
N2 Co1 O1 170.88(10) 3_665 2_655 ?
N2 Co1 O1 90.03(10) . 2_655 ?
O1 Co1 O1 81.77(9) . 2_655 ?
O1 Co1 O1 81.77(9) 3_665 2_655 ?
N2 Co1 Co2 122.07(8) 2_655 . ?
N2 Co1 Co2 122.07(8) 3_665 . ?
N2 Co1 Co2 122.07(8) . . ?
O1 Co1 Co2 49.10(6) . . ?
O1 Co1 Co2 49.09(6) 3_665 . ?
O1 Co1 Co2 49.09(6) 2_655 . ?
C1 O1 Co1 126.93(19) . . ?
C1 O1 Co2 137.27(19) . . ?
Co1 O1 Co2 86.95(8) . . ?
O1 C1 C2 118.1(3) . . ?
O1 C1 C6 122.3(3) . . ?
C2 C1 C6 119.6(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 C7 119.9(3) . . ?
C1 C6 C7 121.6(3) . . ?
N2 C7 N1 112.9(3) . . ?
N2 C7 C6 125.3(3) . . ?
N1 C7 C6 121.7(3) . . ?
C7 N1 C8 109.8(3) . . ?
C7 N1 H1 122(3) . . ?
C8 N1 H1 121(3) . . ?
N1 C8 C9 100.9(2) . . ?
N1 C8 H8 111.6 . . ?
C9 C8 H8 111.6 . . ?
N1 C8 H8A 111.6 . . ?
C9 C8 H8A 111.6 . . ?
H8 C8 H8A 109.4 . . ?
N2 C9 C8 104.2(2) . . ?
N2 C9 H9 110.9 . . ?
C8 C9 H9 110.9 . . ?
N2 C9 H9A 110.9 . . ?
C8 C9 H9A 110.9 . . ?
H9 C9 H9A 108.9 . . ?
C7 N2 C9 108.4(2) . . ?
C7 N2 Co1 125.7(2) . . ?
C9 N2 Co1 123.88(19) . . ?
O1 Co2 O1 73.91(9) 17 18_545 ?
O1 Co2 O1 73.91(9) 17 16_655 ?
O1 Co2 O1 73.91(9) 18_545 16_655 ?
O1 Co2 O1 180.0 17 2_655 ?
O1 Co2 O1 106.09(9) 18_545 2_655 ?
O1 Co2 O1 106.09(9) 16_655 2_655 ?
O1 Co2 O1 106.09(9) 17 3_665 ?
O1 Co2 O1 180.0 18_545 3_665 ?
O1 Co2 O1 106.09(9) 16_655 3_665 ?
O1 Co2 O1 73.90(9) 2_655 3_665 ?
O1 Co2 O1 106.10(9) 17 . ?
O1 Co2 O1 106.10(9) 18_545 . ?
O1 Co2 O1 180.0 16_655 . ?
O1 Co2 O1 73.90(9) 2_655 . ?
O1 Co2 O1 73.90(9) 3_665 . ?
O1 Co2 Co1 43.96(6) 17 16_655 ?
O1 Co2 Co1 43.96(6) 18_545 16_655 ?
O1 Co2 Co1 43.96(6) 16_655 16_655 ?
O1 Co2 Co1 136.04(6) 2_655 16_655 ?
O1 Co2 Co1 136.04(6) 3_665 16_655 ?
O1 Co2 Co1 136.05(6) . 16_655 ?
O1 Co2 Co1 136.04(6) 17 . ?
O1 Co2 Co1 136.04(6) 18_545 . ?
O1 Co2 Co1 136.04(6) 16_655 . ?
O1 Co2 Co1 43.96(6) 2_655 . ?
O1 Co2 Co1 43.96(6) 3_665 . ?
O1 Co2 Co1 43.96(6) . . ?
Co1 Co2 Co1 180.0 16_655 . ?
O2 C10 O2 97.6(19) 2_545 . ?
O2 C10 H10 95.4 2_545 . ?
O2 C10 H10 109.5 . . ?
O2 C10 H10A 133.4 2_545 . ?
O2 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
O2 C10 H10B 24.0 2_545 . ?
O2 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C10 O2 H2M 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 C1 C2 -158.4(2) . . . . ?
Co2 O1 C1 C2 66.0(4) . . . . ?
Co1 O1 C1 C6 21.2(4) . . . . ?
Co2 O1 C1 C6 -114.5(3) . . . . ?
O1 C1 C2 C3 178.0(3) . . . . ?
C6 C1 C2 C3 -1.5(5) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
C3 C4 C5 C6 -1.5(6) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C4 C5 C6 C7 -177.7(3) . . . . ?
O1 C1 C6 C5 -178.7(3) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
O1 C1 C6 C7 -0.3(5) . . . . ?
C2 C1 C6 C7 179.2(3) . . . . ?
C5 C6 C7 N2 160.4(3) . . . . ?
C1 C6 C7 N2 -17.9(5) . . . . ?
C5 C6 C7 N1 -18.7(5) . . . . ?
C1 C6 C7 N1 162.9(3) . . . . ?
N2 C7 N1 C8 -9.8(4) . . . . ?
C6 C7 N1 C8 169.4(3) . . . . ?
C7 N1 C8 C9 17.4(3) . . . . ?
N1 C8 C9 N2 -18.2(3) . . . . ?
N1 C7 N2 C9 -3.2(4) . . . . ?
C6 C7 N2 C9 177.6(3) . . . . ?
N1 C7 N2 Co1 -167.5(2) . . . . ?
C6 C7 N2 Co1 13.4(4) . . . . ?
C8 C9 N2 C7 14.0(3) . . . . ?
C8 C9 N2 Co1 178.6(2) . . . . ?
N2 Co1 N2 C7 178.5(2) 2_655 . . . ?
N2 Co1 N2 C7 -86.7(3) 3_665 . . . ?
O1 Co1 N2 C7 3.5(3) . . . . ?
O1 Co1 N2 C7 85.3(3) 2_655 . . . ?
Co2 Co1 N2 C7 45.9(3) . . . . ?
N2 Co1 N2 C9 16.5(3) 2_655 . . . ?
N2 Co1 N2 C9 111.33(18) 3_665 . . . ?
O1 Co1 N2 C9 -158.4(2) . . . . ?
O1 Co1 N2 C9 -76.6(2) 2_655 . . . ?
Co2 Co1 N2 C9 -116.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl1 0.71(4) 2.44(4) 3.122(3) 160(4) .

_refine_diff_density_max         0.657
_refine_diff_density_min         -1.241
_refine_diff_density_rms         0.109

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_0721171m_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 1848339'
_audit_update_record             
;
2018-06-09 deposited with the CCDC.
2018-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H54 Co3 N12 O6, 2(Br), 2(C H4 O)'
_chemical_formula_sum            'C56 H62 Br2 Co3 N12 O8'
_chemical_formula_weight         1367.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'

_cell_length_a                   11.0654(11)
_cell_length_b                   11.0654(11)
_cell_length_c                   87.132(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     9239(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    2235
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      28.01

_exptl_crystal_description       platelet
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             4182
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.157
_shelx_estimated_absorpt_T_min   0.626
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18737
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -116
_diffrn_reflns_limit_l_max       104
_diffrn_reflns_theta_min         2.831
_diffrn_reflns_theta_max         28.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2589
_reflns_number_gt                1878
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+106.5615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2589
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0766
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_restrained_S_all      1.224
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 1.0000 1.0000 0.53157(2) 0.0161(2) Uani 1 3 d S T P . .
Co2 Co 1.0000 1.0000 0.5000 0.0146(3) Uani 1 6 d S T P . .
Br1 Br 0.3333 0.6667 0.57207(2) 0.0235(2) Uani 1 3 d S T P . .
O1 O 0.8992(3) 1.0466(3) 0.51722(3) 0.0142(7) Uani 1 1 d . . . . .
C1 C 0.7754(5) 1.0359(4) 0.51937(5) 0.0159(9) Uani 1 1 d . . . . .
C2 C 0.7381(5) 1.1133(5) 0.50987(6) 0.0195(10) Uani 1 1 d . . . . .
H2 H 0.7999 1.1688 0.5019 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6129(5) 1.1109(5) 0.51177(6) 0.0244(11) Uani 1 1 d . . . . .
H3 H 0.5896 1.1651 0.5052 0.029 Uiso 1 1 calc R U . . .
C4 C 0.5211(6) 1.0292(5) 0.52323(6) 0.0283(11) Uani 1 1 d . . . . .
H4 H 0.4356 1.0285 0.5246 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5532(5) 0.9502(5) 0.53249(6) 0.0237(11) Uani 1 1 d . . . . .
H5 H 0.4885 0.8933 0.5401 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6805(5) 0.9512(5) 0.53097(5) 0.0191(10) Uani 1 1 d . . . . .
C7 C 0.7136(5) 0.8698(5) 0.54135(5) 0.0181(9) Uani 1 1 d . . . . .
N1 N 0.6167(5) 0.7671(4) 0.55025(5) 0.0231(9) Uani 1 1 d . . . . .
C8 C 0.6840(6) 0.7242(6) 0.56163(6) 0.0317(13) Uani 1 1 d . . . . .
H8 H 0.6362 0.6214 0.5626 0.038 Uiso 1 1 calc R U . . .
H8A H 0.6868 0.7652 0.5718 0.038 Uiso 1 1 calc R U . . .
C9 C 0.8290(5) 0.7825(5) 0.55498(6) 0.0219(10) Uani 1 1 d . . . . .
H9 H 0.9011 0.8285 0.5630 0.026 Uiso 1 1 calc R U . . .
H9A H 0.8404 0.7079 0.5501 0.026 Uiso 1 1 calc R U . . .
N2 N 0.8384(4) 0.8852(4) 0.54337(4) 0.0174(8) Uani 1 1 d . . . . .
O2 O 0.6678(13) 0.3959(13) 0.60467(15) 0.043(3) Uani 0.3333 1 d . . P A -1
H2A H 0.7506 0.4526 0.6022 0.064 Uiso 0.3333 1 calc R U P A -1
C10 C 0.6667 0.3333 0.61775(13) 0.063(4) Uani 1 3 d S T P . .
H10 H 0.7431 0.3127 0.6177 0.095 Uiso 0.3333 1 calc R U P A .
H10A H 0.5775 0.2462 0.6188 0.095 Uiso 0.3333 1 calc R U P . .
H10B H 0.6786 0.3950 0.6264 0.095 Uiso 0.3333 1 calc R U P . .
H10C H 0.551(5) 0.765(5) 0.5530(5) 0.008(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N2 1.896(4) 3_675 ?
Co1 N2 1.896(4) 2_765 ?
Co1 N2 1.896(4) . ?
Co1 O1 1.910(3) . ?
Co1 O1 1.910(3) 2_765 ?
Co1 O1 1.910(3) 3_675 ?
Co1 Co2 2.7509(10) . ?
Co2 O1 2.083(3) 20_566 ?
Co2 O1 2.083(3) 2_765 ?
Co2 O1 2.083(3) 21_656 ?
Co2 O1 2.083(3) 3_675 ?
Co2 O1 2.083(3) 19_776 ?
Co2 O1 2.083(3) . ?
Co2 Co1 2.7508(10) 19_776 ?
O1 C1 1.328(5) . ?
C1 C2 1.394(6) . ?
C1 C6 1.420(6) . ?
C2 C3 1.382(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.361(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.409(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.448(7) . ?
C7 N2 1.315(6) . ?
C7 N1 1.350(6) . ?
N1 C8 1.455(7) . ?
N1 H10C 0.76(5) . ?
C8 C9 1.513(7) . ?
C8 H8 0.9900 . ?
C8 H8A 0.9900 . ?
C9 N2 1.486(6) . ?
C9 H9 0.9900 . ?
C9 H9A 0.9900 . ?
O2 C10 1.330(14) . ?
O2 H2A 0.8400 . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Co1 N2 93.41(17) 3_675 2_765 ?
N2 Co1 N2 93.41(17) 3_675 . ?
N2 Co1 N2 93.41(17) 2_765 . ?
N2 Co1 O1 91.22(14) 3_675 . ?
N2 Co1 O1 171.82(15) 2_765 . ?
N2 Co1 O1 93.04(14) . . ?
N2 Co1 O1 171.82(15) 3_675 2_765 ?
N2 Co1 O1 93.04(14) 2_765 2_765 ?
N2 Co1 O1 91.22(15) . 2_765 ?
O1 Co1 O1 81.80(14) . 2_765 ?
N2 Co1 O1 93.04(15) 3_675 3_675 ?
N2 Co1 O1 91.22(15) 2_765 3_675 ?
N2 Co1 O1 171.82(16) . 3_675 ?
O1 Co1 O1 81.80(14) . 3_675 ?
O1 Co1 O1 81.80(14) 2_765 3_675 ?
N2 Co1 Co2 122.81(12) 3_675 . ?
N2 Co1 Co2 122.81(12) 2_765 . ?
N2 Co1 Co2 122.81(12) . . ?
O1 Co1 Co2 49.12(9) . . ?
O1 Co1 Co2 49.11(9) 2_765 . ?
O1 Co1 Co2 49.11(9) 3_675 . ?
O1 Co2 O1 180.00(11) 20_566 2_765 ?
O1 Co2 O1 73.83(13) 20_566 21_656 ?
O1 Co2 O1 106.17(13) 2_765 21_656 ?
O1 Co2 O1 106.17(13) 20_566 3_675 ?
O1 Co2 O1 73.83(13) 2_765 3_675 ?
O1 Co2 O1 180.00(11) 21_656 3_675 ?
O1 Co2 O1 73.83(13) 20_566 19_776 ?
O1 Co2 O1 106.17(13) 2_765 19_776 ?
O1 Co2 O1 73.83(13) 21_656 19_776 ?
O1 Co2 O1 106.17(13) 3_675 19_776 ?
O1 Co2 O1 106.18(13) 20_566 . ?
O1 Co2 O1 73.82(13) 2_765 . ?
O1 Co2 O1 106.18(13) 21_656 . ?
O1 Co2 O1 73.82(13) 3_675 . ?
O1 Co2 O1 180.0 19_776 . ?
O1 Co2 Co1 43.91(8) 20_566 19_776 ?
O1 Co2 Co1 136.09(8) 2_765 19_776 ?
O1 Co2 Co1 43.91(9) 21_656 19_776 ?
O1 Co2 Co1 136.09(9) 3_675 19_776 ?
O1 Co2 Co1 43.91(8) 19_776 19_776 ?
O1 Co2 Co1 136.09(8) . 19_776 ?
O1 Co2 Co1 136.09(8) 20_566 . ?
O1 Co2 Co1 43.91(8) 2_765 . ?
O1 Co2 Co1 136.09(9) 21_656 . ?
O1 Co2 Co1 43.91(9) 3_675 . ?
O1 Co2 Co1 136.09(8) 19_776 . ?
O1 Co2 Co1 43.91(8) . . ?
Co1 Co2 Co1 180.0 19_776 . ?
C1 O1 Co1 126.8(3) . . ?
C1 O1 Co2 137.4(3) . . ?
Co1 O1 Co2 86.98(12) . . ?
O1 C1 C2 118.1(4) . . ?
O1 C1 C6 123.3(4) . . ?
C2 C1 C6 118.6(4) . . ?
C3 C2 C1 121.3(5) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 C7 120.0(4) . . ?
C1 C6 C7 121.4(4) . . ?
N2 C7 N1 111.9(4) . . ?
N2 C7 C6 125.4(4) . . ?
N1 C7 C6 122.7(4) . . ?
C7 N1 C8 110.2(4) . . ?
C7 N1 H10C 124(4) . . ?
C8 N1 H10C 115(4) . . ?
N1 C8 C9 101.9(4) . . ?
N1 C8 H8 111.4 . . ?
C9 C8 H8 111.4 . . ?
N1 C8 H8A 111.4 . . ?
C9 C8 H8A 111.4 . . ?
H8 C8 H8A 109.2 . . ?
N2 C9 C8 103.9(4) . . ?
N2 C9 H9 111.0 . . ?
C8 C9 H9 111.0 . . ?
N2 C9 H9A 111.0 . . ?
C8 C9 H9A 111.0 . . ?
H9 C9 H9A 109.0 . . ?
C7 N2 C9 108.9(4) . . ?
C7 N2 Co1 126.3(3) . . ?
C9 N2 Co1 124.3(3) . . ?
C10 O2 H2A 109.5 . . ?
O2 C10 H10 109.5 . . ?
O2 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 C1 C2 160.3(3) . . . . ?
Co2 O1 C1 C2 -64.0(6) . . . . ?
Co1 O1 C1 C6 -18.8(6) . . . . ?
Co2 O1 C1 C6 116.9(5) . . . . ?
O1 C1 C2 C3 -177.8(4) . . . . ?
C6 C1 C2 C3 1.3(7) . . . . ?
C1 C2 C3 C4 -0.6(8) . . . . ?
C2 C3 C4 C5 -0.8(8) . . . . ?
C3 C4 C5 C6 1.4(8) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
C4 C5 C6 C7 177.8(5) . . . . ?
O1 C1 C6 C5 178.4(4) . . . . ?
C2 C1 C6 C5 -0.7(7) . . . . ?
O1 C1 C6 C7 -0.1(7) . . . . ?
C2 C1 C6 C7 -179.2(4) . . . . ?
C5 C6 C7 N2 -164.0(5) . . . . ?
C1 C6 C7 N2 14.4(7) . . . . ?
C5 C6 C7 N1 15.8(7) . . . . ?
C1 C6 C7 N1 -165.7(4) . . . . ?
N2 C7 N1 C8 11.7(6) . . . . ?
C6 C7 N1 C8 -168.2(4) . . . . ?
C7 N1 C8 C9 -17.4(5) . . . . ?
N1 C8 C9 N2 16.3(5) . . . . ?
N1 C7 N2 C9 -0.1(5) . . . . ?
C6 C7 N2 C9 179.8(4) . . . . ?
N1 C7 N2 Co1 171.8(3) . . . . ?
C6 C7 N2 Co1 -8.4(7) . . . . ?
C8 C9 N2 C7 -10.8(5) . . . . ?
C8 C9 N2 Co1 177.2(3) . . . . ?
N2 Co1 N2 C7 85.3(5) 3_675 . . . ?
N2 Co1 N2 C7 178.9(4) 2_765 . . . ?
O1 Co1 N2 C7 -6.1(4) . . . . ?
O1 Co1 N2 C7 -87.9(4) 2_765 . . . ?
Co2 Co1 N2 C7 -47.9(4) . . . . ?
N2 Co1 N2 C9 -104.1(3) 3_675 . . . ?
N2 Co1 N2 C9 -10.4(4) 2_765 . . . ?
O1 Co1 N2 C9 164.5(4) . . . . ?
O1 Co1 N2 C9 82.7(4) 2_765 . . . ?
Co2 Co1 N2 C9 122.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H10C Br1 0.76(5) 2.67(5) 3.346(4) 150(5) .

_refine_diff_density_max         0.857
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.108



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
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data_tu01101m_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 1848340'
_audit_update_record             
;
2018-06-09 deposited with the CCDC.
2018-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H54 Co3 N12 O6, 2(N O3), 2(C H4 O)'
_chemical_formula_sum            'C56 H62 Co3 N14 O14'
_chemical_formula_weight         1331.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'

_cell_length_a                   11.169(3)
_cell_length_b                   11.169(3)
_cell_length_c                   87.48(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     9450(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    3752
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.84

_exptl_crystal_description       platelet
_exptl_crystal_colour            brwon
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             4134
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.853
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_T_max  0.807
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19005
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -78
_diffrn_reflns_limit_l_max       116
_diffrn_reflns_theta_min         2.156
_diffrn_reflns_theta_max         28.535
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2631
_reflns_number_gt                1872
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2631
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.6667 0.3333 0.30216(2) 0.02133(15) Uani 1 3 d S T P . .
O1 O 0.71598(14) 0.48003(15) 0.31645(2) 0.0218(3) Uani 1 1 d . . . . .
C1 C 0.7055(2) 0.5929(2) 0.31446(2) 0.0224(4) Uani 1 1 d . . . . .
C2 C 0.7839(2) 0.7073(2) 0.32390(2) 0.0263(5) Uani 1 1 d . . . . .
H2 H 0.8401 0.7012 0.3317 0.032 Uiso 1 1 calc R U . . .
C3 C 0.7812(2) 0.8281(2) 0.32215(3) 0.0313(5) Uani 1 1 d . . . . .
H3 H 0.8350 0.9043 0.3287 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7000(3) 0.8393(2) 0.31082(3) 0.0347(6) Uani 1 1 d . . . . .
H4 H 0.6994 0.9234 0.3095 0.042 Uiso 1 1 calc R U . . .
C5 C 0.6208(2) 0.7280(2) 0.30156(3) 0.0314(5) Uani 1 1 d . . . . .
H5 H 0.5645 0.7358 0.2939 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6210(2) 0.6028(2) 0.30308(2) 0.0245(5) Uani 1 1 d . . . . .
C7 C 0.5386(2) 0.4883(2) 0.29266(2) 0.0257(5) Uani 1 1 d . . . . .
N1 N 0.4369(2) 0.4850(2) 0.28403(2) 0.0354(5) Uani 1 1 d . . . . .
H1 H 0.420(2) 0.553(3) 0.2830(3) 0.041(8) Uiso 1 1 d . . . . .
C8 C 0.3905(3) 0.3746(3) 0.27287(3) 0.0415(6) Uani 1 1 d . . . . .
H8 H 0.4273 0.4112 0.2626 0.050 Uiso 1 1 calc R U . . .
H8A H 0.2883 0.3199 0.2724 0.050 Uiso 1 1 calc R U . . .
C9 C 0.4506(2) 0.2893(2) 0.27909(3) 0.0342(6) Uani 1 1 d . . . . .
H9 H 0.3780 0.2036 0.2840 0.041 Uiso 1 1 calc R U . . .
H9A H 0.4948 0.2642 0.2709 0.041 Uiso 1 1 calc R U . . .
N2 N 0.55439(18) 0.38114(18) 0.29049(2) 0.0261(4) Uani 1 1 d . . . . .
Co2 Co 0.6667 0.3333 0.3333 0.01670(17) Uani 1 6 d S T P . .
N3 N 0.3333 0.6667 0.26242(4) 0.0223(6) Uani 1 3 d S T P . .
O2 O 0.3333 0.6667 0.27598(4) 0.0423(8) Uani 1 3 d S T P A .
O3 O 0.302(4) 0.570(2) 0.25523(16) 0.114(6) Uani 0.3333 1 d . . P A -1
C10 C 1.0000 1.0000 0.28426(7) 0.0674(17) Uani 1 3 d S T P . .
H10 H 0.9434 0.9335 0.2922 0.101 Uiso 0.3333 1 calc R U P B .
H10A H 0.9590 1.0567 0.2815 0.101 Uiso 0.3333 1 calc R U P . .
H10B H 1.0938 1.0597 0.2882 0.101 Uiso 0.3333 1 calc R U P . .
O7 O 1.0053(13) 0.9309(9) 0.27177(9) 0.094(3) Uani 0.3333 1 d . . P B -1
O4 O 0.355(3) 0.7747(9) 0.25441(11) 0.071(3) Uani 0.3333 1 d . . P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N2 1.8895(19) 2_655 ?
Co1 N2 1.8895(19) 3_665 ?
Co1 N2 1.8896(19) . ?
Co1 O1 1.9094(15) 3_665 ?
Co1 O1 1.9094(15) 2_655 ?
Co1 O1 1.9094(15) . ?
Co1 Co2 2.7266(8) . ?
O1 C1 1.335(2) . ?
O1 Co2 2.0659(14) . ?
C1 C2 1.401(3) . ?
C1 C6 1.413(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.461(3) . ?
C7 N2 1.308(3) . ?
C7 N1 1.349(3) . ?
N1 C8 1.451(3) . ?
N1 H1 0.87(3) . ?
C8 C9 1.514(3) . ?
C8 H8 0.9900 . ?
C8 H8A 0.9900 . ?
C9 N2 1.484(3) . ?
C9 H9 0.9900 . ?
C9 H9A 0.9900 . ?
Co2 O1 2.0657(14) 33_545 ?
Co2 O1 2.0658(15) 32 ?
Co2 O1 2.0658(14) 31_655 ?
Co2 O1 2.0659(14) 3_665 ?
Co2 O1 2.0659(15) 2_655 ?
Co2 Co1 2.7265(9) 31_655 ?
N3 O3 1.144(10) . ?
N3 O2 1.186(4) . ?
N3 O4 1.310(8) . ?
C10 O7 1.356(8) . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Co1 N2 93.54(8) 2_655 3_665 ?
N2 Co1 N2 93.54(8) 2_655 . ?
N2 Co1 N2 93.54(8) 3_665 . ?
N2 Co1 O1 90.74(7) 2_655 3_665 ?
N2 Co1 O1 93.36(7) 3_665 3_665 ?
N2 Co1 O1 171.65(7) . 3_665 ?
N2 Co1 O1 93.36(7) 2_655 2_655 ?
N2 Co1 O1 171.64(7) 3_665 2_655 ?
N2 Co1 O1 90.74(7) . 2_655 ?
O1 Co1 O1 81.84(7) 3_665 2_655 ?
N2 Co1 O1 171.64(7) 2_655 . ?
N2 Co1 O1 90.74(7) 3_665 . ?
N2 Co1 O1 93.36(7) . . ?
O1 Co1 O1 81.83(7) 3_665 . ?
O1 Co1 O1 81.83(7) 2_655 . ?
N2 Co1 Co2 122.72(6) 2_655 . ?
N2 Co1 Co2 122.72(6) 3_665 . ?
N2 Co1 Co2 122.73(6) . . ?
O1 Co1 Co2 49.14(4) 3_665 . ?
O1 Co1 Co2 49.14(4) 2_655 . ?
O1 Co1 Co2 49.14(4) . . ?
C1 O1 Co1 126.97(13) . . ?
C1 O1 Co2 136.70(13) . . ?
Co1 O1 Co2 86.52(6) . . ?
O1 C1 C2 118.35(19) . . ?
O1 C1 C6 122.90(19) . . ?
C2 C1 C6 118.7(2) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 119.9(2) . . ?
C1 C6 C7 121.57(19) . . ?
N2 C7 N1 113.0(2) . . ?
N2 C7 C6 125.28(19) . . ?
N1 C7 C6 121.7(2) . . ?
C7 N1 C8 109.7(2) . . ?
C7 N1 H1 125.2(18) . . ?
C8 N1 H1 122.1(18) . . ?
N1 C8 C9 102.17(19) . . ?
N1 C8 H8 111.3 . . ?
C9 C8 H8 111.3 . . ?
N1 C8 H8A 111.3 . . ?
C9 C8 H8A 111.3 . . ?
H8 C8 H8A 109.2 . . ?
N2 C9 C8 104.21(18) . . ?
N2 C9 H9 110.9 . . ?
C8 C9 H9 110.9 . . ?
N2 C9 H9A 110.9 . . ?
C8 C9 H9A 110.9 . . ?
H9 C9 H9A 108.9 . . ?
C7 N2 C9 108.32(18) . . ?
C7 N2 Co1 126.29(15) . . ?
C9 N2 Co1 124.57(15) . . ?
O1 Co2 O1 74.52(6) 33_545 32 ?
O1 Co2 O1 74.52(6) 33_545 31_655 ?
O1 Co2 O1 74.51(6) 32 31_655 ?
O1 Co2 O1 105.49(6) 33_545 . ?
O1 Co2 O1 105.49(6) 32 . ?
O1 Co2 O1 180.0 31_655 . ?
O1 Co2 O1 180.00(5) 33_545 3_665 ?
O1 Co2 O1 105.49(6) 32 3_665 ?
O1 Co2 O1 105.49(6) 31_655 3_665 ?
O1 Co2 O1 74.51(6) . 3_665 ?
O1 Co2 O1 105.49(6) 33_545 2_655 ?
O1 Co2 O1 180.00(8) 32 2_655 ?
O1 Co2 O1 105.49(6) 31_655 2_655 ?
O1 Co2 O1 74.51(6) . 2_655 ?
O1 Co2 O1 74.51(6) 3_665 2_655 ?
O1 Co2 Co1 135.65(4) 33_545 . ?
O1 Co2 Co1 135.65(4) 32 . ?
O1 Co2 Co1 135.65(4) 31_655 . ?
O1 Co2 Co1 44.35(4) . . ?
O1 Co2 Co1 44.35(4) 3_665 . ?
O1 Co2 Co1 44.35(4) 2_655 . ?
O1 Co2 Co1 44.35(4) 33_545 31_655 ?
O1 Co2 Co1 44.35(4) 32 31_655 ?
O1 Co2 Co1 44.35(4) 31_655 31_655 ?
O1 Co2 Co1 135.65(4) . 31_655 ?
O1 Co2 Co1 135.65(4) 3_665 31_655 ?
O1 Co2 Co1 135.65(4) 2_655 31_655 ?
Co1 Co2 Co1 180.0 . 31_655 ?
O3 N3 O2 123.3(9) . . ?
O3 N3 O4 113.9(6) . . ?
O2 N3 O4 122.3(5) . . ?
O7 C10 H10 109.5 . . ?
O7 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
O7 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 C1 C2 -160.62(14) . . . . ?
Co2 O1 C1 C2 65.9(3) . . . . ?
Co1 O1 C1 C6 18.1(3) . . . . ?
Co2 O1 C1 C6 -115.4(2) . . . . ?
O1 C1 C2 C3 178.0(2) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 -178.0(2) . . . . ?
O1 C1 C6 C5 -177.8(2) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
O1 C1 C6 C7 0.1(3) . . . . ?
C2 C1 C6 C7 178.79(19) . . . . ?
C5 C6 C7 N2 162.9(2) . . . . ?
C1 C6 C7 N2 -14.9(3) . . . . ?
C5 C6 C7 N1 -16.4(3) . . . . ?
C1 C6 C7 N1 165.8(2) . . . . ?
N2 C7 N1 C8 -9.9(3) . . . . ?
C6 C7 N1 C8 169.5(2) . . . . ?
C7 N1 C8 C9 15.4(3) . . . . ?
N1 C8 C9 N2 -15.0(2) . . . . ?
N1 C7 N2 C9 -0.8(3) . . . . ?
C6 C7 N2 C9 179.9(2) . . . . ?
N1 C7 N2 Co1 -170.77(16) . . . . ?
C6 C7 N2 Co1 9.9(3) . . . . ?
C8 C9 N2 C7 10.4(2) . . . . ?
C8 C9 N2 Co1 -179.43(16) . . . . ?
N2 Co1 N2 C7 179.75(18) 2_655 . . . ?
N2 Co1 N2 C7 -86.5(2) 3_665 . . . ?
O1 Co1 N2 C7 86.34(19) 2_655 . . . ?
O1 Co1 N2 C7 4.48(19) . . . . ?
Co2 Co1 N2 C7 46.6(2) . . . . ?
N2 Co1 N2 C9 11.31(19) 2_655 . . . ?
N2 Co1 N2 C9 105.08(14) 3_665 . . . ?
O1 Co1 N2 C9 -82.11(18) 2_655 . . . ?
O1 Co1 N2 C9 -163.97(18) . . . . ?
Co2 Co1 N2 C9 -121.81(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.87(3) 2.04(3) 2.880(2) 161(2) .


_refine_diff_density_max         0.561
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.071



